The glove, which inspired countless copycats, quips and Halloween costumes after it was unveiled in the 1983 video for Jackson's hit "Billie Jean," will be part of a five-day auction next year, Julien's Auctions announced Wednesday.
Jackson is also unloading the grandiose gates that once led to his Neverland Ranch, along with more than 2,000 other personal items.
The King of Pop's possessions will be on display before the auction begins on April 21, 2009. Bids will be accepted in person and online. The sale is to be broadcast live on Auction Network.
Jackson plans to donate a portion of the proceeds to MusiCares, a charitable organization founded by the Recording Academy to help musicians in need.
The singer has been plagued by financial woes since he was acquitted of child-molestation charges in 2003. He went into default on his sprawling Neverland property earlier this year, before an investment company bought the loan. Last month, Jackson's lawyers reached a settlement in a $7 million breach-of-contract case brought by a Bahraini sheik.
As Jackson marked his milestone 50th birthday in August, the reclusive star hinted that he would be back to work eventually.
"(I'm) looking forward to doing a lot of great things," he told ABC News. "I think the best is yet to come in my true humble opinion."